Hydrazine → 2-Methyl-4-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenol

HRID 2375388Notes

Reaction equation

HRID 2375388 reaction equation
[C:1]([C:4]1[C:5]([C:19](=O)[CH3:20])=[C:6]([CH3:18])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH3:17])[CH:11]=2)[C:8]=1[CH3:9])(=O)[CH3:2].[NH2:22][NH2:23]>C(O)C>[CH3:17][C:12]1[CH:11]=[C:10]([N:7]2[C:8]([CH3:9])=[C:4]3[C:5]([C:19]([CH3:20])=[N:22][N:23]=[C:1]3[CH3:2])=[C:6]2[CH3:18])[CH:15]=[CH:14][C:13]=1[OH:16]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 692754081-[4-acetyl-1-(4-hydroxy-3-methyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone

Product 1

HCID 100622612-Methyl-4-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[4-acetyl-1-(4-hydroxy-3-methyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (100 mg, 0.32 mmol) in ethanol (5 mL) was added hydrazine (20 μL). After stirring at rt for 1 h, the reaction mixture was poured into ice water (25 mL). The resulting precipitate was filtered, washed with diethyl ether (20 mL), and then dried under vacuum to afford 2-methyl-4-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenol as a pale yellow solid: 1H NMR (CD3OD, 500 MHz) δ 7.09 (d, 1H), 7.03 (s, 1H), 6.97 (d, 1H), 3.00 (s, 6H), 2.59 (s, 6H), 2.34 (s, 3H); MS (ESI) 282 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with diethyl ether (20 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-5908d089506e4082ab68a192aa4c84ca
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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